92855-64-6

Basic information

• Product Name: 6-Benzyloxyindole-3-carboxaldehyde
• Synonyms: 6-BENZYLOXYINDOLE-3-ALDEHYDE;6-BENZYLOXYINDOLE-3-CARBALDEHYDE;6-BENZYLOXYINDOLE-3-CARBOXALDEHYDE;6-(BENZYLOXY)-1H-INDOLE-3-CARBALDEHYDE;6-Benzyloxyindole-3-carboxaldehyde 98%;6-Benzyloxy-;Zinc02516297;6-Benzyloxy-1H-indole-3-carboxaldehyde 98%
• CAS NO: 92855-64-6
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.28
• Product Categories: Indoles and derivatives;Indoline & Oxindole
• Mol File: 92855-64-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 215-216 °C
• Boiling Point: 474.156 °C at 760 mmHg
• Flash Point: 240.561 °C
• Appearance: /
• Density: 1.267 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 15.67±0.30(Predicted)
• CAS DataBase Reference: 6-Benzyloxyindole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Benzyloxyindole-3-carboxaldehyde(92855-64-6)
• EPA Substance Registry System: 6-Benzyloxyindole-3-carboxaldehyde(92855-64-6)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 92855-64-6(Hazardous Substances Data)

Usage

General Description

6-Benzyloxyindole-3-carboxaldehyde is a chemical compound that belongs to the class of indole derivatives. It is a heterocyclic compound with a benzene ring attached to the oxygen and nitrogen atoms of the indole ring. 6-Benzyloxyindole-3-carboxaldehyde has potential applications in organic synthesis and drug development due to its versatile reactivity and biological activity. It can be used as a building block in the synthesis of various bioactive compounds, pharmaceuticals, and agrochemicals. Additionally, its unique structure and reactivity make it an important intermediate in the production of diverse chemical compounds and materials.

InChI:InChI=1/C16H13NO2/c18-10-13-9-17-16-8-14(6-7-15(13)16)19-11-12-4-2-1-3-5-12/h1-10,17H,11H2

Upstream product

• 15903-94-3 6-benzyloxy-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 141834-88-0 N-methyl-N-phenethyl-2-[(6-benzyloxy-3-formyl)indol-1-yl]acetamide 
• 630110-71-3 6-benzyloxy-1H-1-tert-butoxycarbonylindole-3-carbaldehyde 

Relevant articles and documents

Iodine-Mediated Tryptathionine Formation Facilitates the Synthesis of Amanitins

Synthetic methods on the macrocyclization of peptides are of high interest since they facilitate the synthesis of various types of potentially bioactive compounds, e.g. addressing targets like protein-protein-interactions. Herein, we report on an efficient method to construct tryptathionine-cross-links in peptides between the amino acids Trp and Cys. This reaction not only is the basis for the total synthesis of the death cap toxin α-amanitin but also provides rapid access to various new amanitin analogues. This study for the first time presents a systematic compilation of structure-activity relations (SAR) of amatoxins with regard to RNA polymerase II inhibition and cytotoxicity with one amanitin derivative of superior RNAP II inhibition. The present approach paves the way for the synthesis of structurally diverse amatoxins as future payloads for antibody-toxin conjugates in cancer therapy.

An Enantioselective Total Synthesis of (+)-Duocarmycin SA

An efficient, concise enantioselective total synthesis of the potent antitumor antibiotic (+)-duocarmycin SA is described. The invented route is based on a disconnection strategy that was devised to facilitate rapid and efficient synthesis of key core compounds to enable preclinical structure-activity relationship investigations. The key tricycle core was constructed with a highly enantioselective indole hydrogenation to set the stereocenter and a subsequent hitherto unexplored vicarious, nucleophilic-substitution/cyclization sequence to effectively forge a final indole ring. Additionally, the development of a stable sulfonamide protecting group capable of mild chemoselective cleavage greatly enhanced sequence yield and throughput. An understanding of key reaction parameters ensured a robust, reproducible sequence easily executable on decagram scales to this highly promising class of compounds.

Synthesis of indolyl-3-acetonitrile derivatives and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

Arvelexin is one of major constituents of Brassica rapa that exerts anti-inflammatory activities. Several indolyl-3-acetonitrile derivatives were synthesized as arvelexin analogs and evaluated for their abilities to inhibit NO and PGE2 productions in LPS-induced RAW 264.7 cells. Of the indolyl-3-acetonitriles synthesized, compound 2k, which possesses a hydroxyl group at C-7 position of the indole ring and an N-methyl substituent, more potently inhibited NO and PGE2 productions and was less cytotoxic than arvelexin on macrophage cells.